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The Biosynthesis and Catabolism of the Maleic Anhydride Moiety of Stipitatonic Acid
Author(s) -
al Fahad Ahmed,
Abood Amira,
Simpson Thomas J.,
Cox Russell J.
Publication year - 2014
Publication title -
angewandte chemie
Language(s) - English
Resource type - Journals
eISSN - 1521-3757
pISSN - 0044-8249
DOI - 10.1002/ange.201403450
Subject(s) - moiety , maleic anhydride , decarboxylation , chemistry , biosynthesis , catabolism , aldehyde , organic chemistry , stereochemistry , enzyme , catalysis , biochemistry , polymer , copolymer
Abstract A series of directed knockout experiments, combined with an in vitro assay of pathway components, has elucidated for the first time the chemical steps involved in the biosynthesis of the tropolone class of fungal maleic anhydrides. The pathway involves the stepwise oxidation of aldehyde and methyl carbon atoms to form a 1,2‐dicarboxylate. A hydrolase‐catalyzed interconversion of this and the corresponding maleic anhydride, followed by decarboxylation of the diacid leads to the pathway’s final product of stipitatic acid.